Ponyville After School

(Vectors by jhayarr23, & RainbowRage12

~ ✭ ~

"Okay, you can put away your notebooks, everypony," Miss Cheerilee said. "Now, before you all leave for lunch, please come pick up your copy of yesterday's writing assignment, so we can officially announce the filly or colt of the week!"

Sitting at her desk near the rear end of the class, Toola Roola anxiously bit her lip. She glanced at the board where Cheerilee kept track of everypony's score: Toola Roola was in the lead, having more stars pinned to her name than anypony else in class. She'd come so close so many times, but now it could finally be her turn.

Her nervousness stemmed from how little advance she had over some of the other foals. Silver Spoon, in particular, had only one star less than her, and Miss Cheerilee had announced the top three grades on the writing test would earn two stars each. Silver Spoon always was at the top of the class in writing, so Toola Roola needed to earn some stars too to keep her prize.

Her friend, Coconut Cream, gently nudged her, and Toola Roola snapped out of her thoughts. Nearly all the foals were already in line to pick up their copy, so she rushed to take her place.

"I'm sure you did great, Toola," Coconut said as they waited for their turn. "You'll win for sure!"

Toola Roola wasn't convinced. "If you say so…"

"Of course you will," her friend assured, grinning, "and tonight you'll get to sleep with one super handsome stallion. You'll see!"

Suddenly very uncomfortable, Toola let out an awkward little laugh. "Haha… ha… yes, stallion, of course." She looked away. They reached Miss Cheerilee's desk, and Toola Roola searched for her copy in the few that remained. Finding it quickly, the filly anxiously read the note penned in the margin by the teacher.

19/20
Well done, Toola!
+2 pins

Toola Roola stared at it for a moment, its meaning making its way in her brain. She grinned, and jumped in joy, shouting "YES!"

At her desk, Silver Spoon scowled, visibly disappointed.

A few minutes later, as fillies and colts left class for lunch break, Toola Roola stayed behind with Miss Cheerilee, the filly grinning from ear to ear.

"Congratulations, Toola Roola!" the schoolteacher said, a warm smile on her face. "Here's the list of mares and stallions who are available tonight. Take a few minutes to think about it, then tell me once you made your choice."

Toola nodded, picking up the list and sitting down. Over a dozen names were written on the sheet in two columns, one for stallions and one for mares. There was no other information about these ponies, but it hardly mattered: Ponyville was a pretty small town, and the filly already knew everypony on the list.

Which left the matter of deciding who she wanted to spend the night with. Toola Roola passed through every stallion's name, but, honestly, none really caught her interest. Nervously nibbling her lower lip, she glanced at the second column. There were some really pretty mares on that list, including some big names such as Pinkie Pie and Rainbow Dash, and it made her heart throb. Unable to decide, Toola Roola eventually settled mostly at random on one pony, Amethyst Star, an unicorn mare who lived on her street.

Bashfully, Toola announced her choice to Miss Cheerilee. The teacher only smiled. "Of course, Toola Roola. Go ahead and join your friends for lunch. I'll inform Amethyst so she knows to pick you up after school."

~ ✭ ~

Amethyst Star arrived a bit late at school, which suited Toola Roola just fine. When the mare eventually showed up, Toola was alone with Miss Cheerilee, the rest of the class having already left for the weekend, sparing the filly from having to face her classmates' unavoidable questions.

Amethyst apologised for the delay, shared a quick word with Miss Cheerilee, then left school with Toola. What she didn't tell the filly was that she had been late on purpose: Cheerilee had explained Toola seemed anxious about choosing somepony of the same sex, and neither mares wanted to make the filly uncomfortable in front of her classmates.

It was just a short trot from the school to Amethyst's home. The unicorn welcomed her young guest inside, inviting her to sit down on the couch.

"Well, Toola, Cheerilee told me you're a really good student, and that you worked extra hard this week," Amethyst Star said, smiling kindly. "So, what can I do for you?"

Blushing, Toola Roola looked at the pretty mare in front of her. Amethyst Star was an energetic young mare with a magenta coat, purple eyes and a two-toned violet mane, her cutie mark consisting of three diamonds. Eventually, the filly managed to stammer out a weak "Erm… I dunno…"

Amethyst's expression morphed to concern. "We don't have to do anything if you don't want to," she assured. "Let's just stick to something you're comfortable with for now, okay?"

"O-Okay."

"Why don't we go outside and enjoy this beautiful weather together? I have a pool in the backyard, and we can sit down, share a smoothie."

Toola's nervousness abated at the proposition, and she nodded, smiling. "Sure!"

Ten minutes later, Toola Roola was lounging by the pool, taking in the sun and sipping a fruit smoothie, Amethyst doing the same a few feet from her. That was really nice, actually, letting the filly relax with the unicorn before going any further with her. And Toola wanted more; her gaze kept falling on Amethyst Star's rump, making her oddly warm inside. Still, she was okay with taking it slow.

Amethyst lifted her sunglasses, glancing at Toola Roola. "You know, I like your mane and tail."

"You do?" The filly looked at herself. Her mane was pink, red, and yellow, yet her tail was blue and cyan, creating an odd mismatch.

"Yeah, it's cool! Do you dye your hair?"

Toola Roola shook her head. "Nuh-uh. That's my natural colors. Doctors say it's genetic. It's pretty rare, and, even then, it's generally not that extreme. I've never met anypony else like me." She hesitated, unsure whether she was sad or proud about it.

"Wow, you're a special little filly, Toola. I hope you know that."

Toola Roola took another sip of her drink, shyly dodging the need to respond. She was blushing, but she had to admit it felt really nice to be complimented like that by a mare.

A comfortable silence settled once more in Amethyst's backyard.

Mare and filly spent the remainder of the afternoon like this, occasionally trading words and getting to know each other better. Amethyst had done a lot of interesting things, including being the Animal Team leader during seasonal wrap-ups, and having organized Cranky and Matilda's wedding. Toola Roola talked about her passion for art, and how it had earned her swirling paint brush cutie mark.

Around 6PM, Toola Roola helped set up the table while Amethyst grilled spicy veggies on the barbecue. Dinner was really good, and, after her second serving, the filly slumped at the table, completely stuffed, eliciting a giggle from the unicorn.

“Hehe, I’m glad you liked it!” Amethyst said, smirking. “Why don’t you lay down on the couch while I clean up? I’ll be with you in a minute.”

Toola Roola nodded. “Yeah… thanks.” She dragged her way back to the living room and dropped head first on the comfy couch, feeling very drowsy.

As promised, Amethyst joined her soon after. “Mind if I sit with you?”

The filly stirred, shook her head, and scooched sideways, making some space. The couch wasn’t big, but Amethyst sat closer to Toola than she strictly needed to. That was just fine, though; the filly tentatively snuggled the unicorn, and received a warm hug in return, Amethyst gently stroking her mane. It was more of a sisterly cuddle than a lovers' embrace, but Toola nonetheless enjoyed the mare's tender touch.

"So, Toola Roola, pardon me for asking, but… you like other fillies, is that right?"

"Mmhmm, yeah. I mean… colts are okay, I guess, but… um… I've always known I loved fillies," the filly answered, actually quite comfortable being petted like this.

"Do you have a fillyfriend?"

"No…" Toola's expression turned sullen. "I told my parents, but my friends don't even know. That's why I was glad to be with a mare tonight, but… uh, I have no idea what to do. I guess I'm kinda making a fool of myself…"

With her hoof, Amethyst lifted the filly's chin. "No, you don't. There's nothing wrong with taking it slow. You shouldn't feel pressured. Besides, to be honest with you, I've had a few coltfriends over the years, but I've never been with another girl before, so I don't know what to do either."

"Oh…"

"But that's okay: we can just discover it together. What do you say?"

Toola Roola smiled, then bit her lip. "Um, can I… erm… kiss you?"

"Mmhmm." Amethyst closed her eyes, offering her lips. There was a short pause, then soft filly lips pressed on her mouth. The unicorn moaned appreciatively, wrapping her forelegs around Toola's withers and pulling the filly into a hug. It was over soon, just a shy little kiss by a tender young amateur. Toola Roola, however, seemed completely dazed, which amused her older partner. Taking charge, Amethyst kissed the filly again, putting more force into it, eliciting a throaty purr from her.

It felt really good for the mare too, actually. Kissing the foal, Amethyst's experience from half a dozen coltfriends kicked into gear, and she naturally opened her maw, inviting her partner inside. Nothing came however, reminding the unicorn that she was kissing a shy, inexperienced filly, not a stallion.

Realizing she had to lead, Amethyst gently prodded Toola's mouth with the tip of her tongue, licking her teeth. The filly shuddered, and relaxed her jaw, letting the mare's tongue slip into her muzzle. Caressing Toola's mane, Amethyst explored her mouth, playing with the filly's tongue.

They made out for a while, until Amethyst finally pulled back, letting them both catch their breaths. Toola Roola was in bliss. "Woah…" She licked her lips, just to make sure it was actually real.

"Yeah… That was very good, especially for your first kiss!"

The filly's light blue eyes sparkled. "Really? You liked it?"

"Mmhmm! You're going to make a lucky filly very happy one day. Here…" Amethyst hugged the foal and kissed her again, feeling her little body tremble in her hooves.

As she pressed Toola's body closer, Amethyst felt a distinctive wetness under the filly's mismatched blue tail. That, and the fact that she had to twist her neck uncomfortably to reach the filly sitting next to her, made the unicorn pull back. "Wanna go to my bedroom?" Amethyst asked, caressing her cute rump.

"Y-Yeah… Please!" Toola Roola followed Amethyst Star upstairs.

As she made her way up, the unicorn could practically feel the filly's stare on her rump. She politely lifted her tail, letting her young onlooker peek at her sex. Amethyst had never been particularly interested in other mares, preferring stallions instead, but she had to admit it was quite exciting to be eliciting such desire in Toola.

Entering her bedroom, Amethyst peeked behind her. Though she was already blushing, Toola Roola turned scarlet, and immediately looked away, like she’d been caught staring. Amused, the unicorn mounted the bed, and invited the filly to join her. Toola gingerly climbed atop the bedsheets. As she tried to settle down at Amethyst's side, the unicorn instead redirected the filly behind her, lifting her tail high and exposing her marehood. Toola Roola's eyes opened wide, her mouth forming a perfect O.

Amethyst wiggled her rump. "Don't be shy, Toola. Take your time and explore me. I'm not going anywhere."

"O-Okay." Toola Roola took in the breathtaking sight of the mare's genitalia. She'd seen under other fillies' tails, of course, and she had thoroughly explored her own sex, but never had she had access to somepony's else like this before. Under the hairless dock of Amethyst's tail laid the pert pucker of her anus. Her vulva started right underneath, the magenta lips of her labia narrow near the top but wider near the bottom, forming the classical shape of a raindrop.

Secretly, Toola Roola had always being disappointed in her own fillyhood: it was not particularly symmetrical, and there was little wrinkles near her tailhole. Examining Amethyst's vulva, however, the filly realized that — though the mare's sex was different from her own — it wasn't 'perfect' either… and, for all its little irregularities, it was still astonishingly beautiful. It made her feel a lot better about her own body, and curious to see more, Toola brought her forehoof to Amethyst's sex, though she stopped short of actually coming in contact with her. She lifted her head to look past the mare's rump. "Uh… Miss Amethyst? Can I… you know… touch your… erm…"

The unicorn chuckled. "Sure, you can do whatever you want." She winked. "As long as you don't bite anything."

"Hehe! I won't!" Going back to the mare's pussy, Toola carefully, almost reverently, parted the folds of Amethyst's labia, revealing the pink insides of her sex. The mare shivered cutely from the filly's touch, making Toola smile.

Near the top of her sex, the entrance of Amethyst's vagina offered an enticing view inside her. The smooth inner skin had a clear, wet sheen to it. Toola blinked a few times; was she actually managing to make a grown mare feel good? At the bottom of the slit, Amethyst's clit gently pulsed. Intrigued, Toola carefully poked the little nub. The unicorn moaned softly, her vulva winking and her hindlegs twitching.

Huh… Emboldened by the reaction, the filly delicately caressed Amethyst's clitoris. The mare moaned some more, wiggling her tail. Toola rubbed Amethyst's marehood a little more forcefully.

"Mmmh! Yes!"

Toola Roola's hoof was slick, coated in Amethyst's clear fluids. The mare gasped and cooed, shaking as she was masturbated by a little filly hoof. Her vulva bloomed, red and puffy with arousal. Toola took in the pungent scent of an excited mare. Her own fillyhood kept winking, throbbing with need, but she paid it no mind; Amethyst Star's pleasure was filling her with a heady thrill, something the young filly had never felt before.

"A-Aaah… unf! U-Use your tongue, m-maybe? Please~"

Toola Roola stared wide eyed at Amethyst's needy pussy, considering that enticing possibility. She'd heard about this, sure — some ponies called it 'eating out' a mare — but she had always thought it was kind of gross. Why would anypony want to put their mouth there? That's where mares peed from! And yet, with her mind drowning in hazy lust, Amethyst's excited vulva filling her sight, it suddenly didn't seem so icky anymore.

With just the tip of her tongue, Toola licked Amethyst's open sex, getting her first taste ever of another girl's vulva. It tasted kinda tangy, and smelled really strong, but it wasn't bad. Somewhere in that bouquet of musky flavors, the filly could discern the subtle, intoxicating undertones of Amethyst's breeding pheromones.

Wanting more, Toola pressed a bit more with her tongue. Amethyst squirmed in response, pushing back with her pelvis, driving the filly's muzzle deeper inside her sex. As Toola licked the unicorn's pussy, her tongue unwittingly slipped inside her vagina, plunging deep into the mare. Interestingly, Amethyst Star's foal-canal contracted rhythmically around Toola Roola's tongue, naturally trying to help her inside the tight passage.

As she explored every nook of a mare's vagina she could reach, her vision filled with Amethyst's cute purple anus, Toola felt the unicorn's clit poke her chin. Not wanting to give up her oral spelunking, the filly brought back her hoof again, masturbating the mare… to spectacular results. "Oh, buck me!" Amethyst yelled, a spasm coursing through her spine.

Her face soaked in mare juices, Toola grinned, excited. She could practically sense the climax building in the unicorn's body. With her free forehoof, Toola held Amethyst Star's beautiful rump in place as she relentlessly stimulated her marehood. Her tongue was tiring out, but she was a tough filly: she wouldn't stop, not when her partner was this close to her release.

Amethyst Star went absolutely rigid, all her muscles tensing as she came from the filly dual touch. A strangled, weak cry escaped her throat, sounding almost like she was about to sob. Toola Roola suckled on her clit, the little nub throbbing in her mouth, until, finally, creamy, yellowish marecum gushed all over her filly face.

Toola valiantly suckled the mare's clit, prolonging her orgasm until, eventually, she couldn’t hold on anymore. The filly backed out, gasping for breath, her little heart thumping in her chest. She fell limp on the bedsheet, as did Amethyst. For a while, they both laid where they were, panting heavily.

Amethyst rolled on her back, seeing stars. "Holy… bucking… Celestia…" she muttered to herself. She lifted her head to check beyond her heaving tummy; Toola Roola laid beside her tail, visibly recovering from the exertion. A surge of embarrassment swelled within her as she noticed the poor filly's face was soiled with several globs of her own creamy emissions, one even dripping from her tricolor mane.

"Uh, sorry 'bout that, kid," Amethyst said nervously. Using her magic, she levitated a towel from her wardrobe and thoroughly wiped Toola's face until the filly was reasonably clean.

Toola Roola let it happen. In fact, she barely noticed. A single, triumphant thought occupied her mind: she'd made Amethyst cum. She, a little filly, had made a grown mare orgasm. It drowned out everything else, even the insistent throbbing of her own needy pussy.

"Wow, you… That was really good, Toola…" Amethyst let out, her tone carrying a distinct note of shock.

The filly retreated behind her bangs, flustered by the compliment. "Uh, you really think so?"

"Yeah! Are you sure you've never done this before?"

Toola shook her head. "Nuh-uh…"

Amethyst Star stared at the young filly in disbelief. In truth, the unicorn was astounded: she'd been with a few stallions before, but none of them had been able to make her cum just with oral, and yet that little girl had done it like a pro… on her first try.

Taking a deep breath and shaking her head to clear her thoughts, Amethyst realized she had not done her job of pleasing the filly, something that Toola — if the wet stain under her tail and the quivering of her rump were any indications — badly needed.

Amethyst's first orgasm had fed her arousal more than it had quenched it. She looked down on the excited filly, her expression almost hungry. "Hey, wanna try something with me?"

"I… um… sure…?"

Without warning, Amethyst pounced on Toola Roola, locking her lips on hers and sending her tumbling backward. She pinned down the filly, taking advantage of her surprised yelp to push her tongue in her muzzle, tasting her own tanginess. Toola squirmed for a moment in confusion, then relaxed, submitting to the unicorn.

Grabbing Toola's rump, she pressed the filly's crotch on her underbarrel, rubbing her excited clitoris in her fur. Not breaking the kiss, Amethyst started a slow back and forth, moving up and down the filly almost like a mating stallion would. Toola Roola moaned into the kiss, her fillyhood finally getting the attention it deserved.

When she eventually pulled back from the filly's mouth, Amethyst moved up until both of their crotches rubbed together, their flat, immature teats kissing each other. Her forelegs straight, hooves on either side of Toola's head, Amethyst towered over the panting filly, putting most of her weight on her pelvis.

In spite of her lust, Amethyst Star needed to take a moment to plan her next move. While she had some notions regarding mare-on-mare sex, she had never done anything like this, and the position required some careful maneuvering. First, she moved back, keeping her crotch in position until she was practically falling backward, having to twist her forelegs to support herself. Then, she passed one of her hindlegs over one of Toola Roola's own.

"Erm, what are you doing?" Toola asked, struggling to get a better view.

"Shh, don't move. I got this. Just… have to… Aaah! There!"

Mare and filly moaned in unison, their vulvas sharing the most intimate of kisses. Amethyst shuddered, feeling Toola Roola's clit rub her own sensitive nub

"W-Woah!" Wide eyed, Toola stared at where their bodies met, Amethyst's plush labia entering her blooming slit.

The unicorn smiled. "Heh… That's called 'scissoring'. I heard it's a great way for two girl to have sex, and… unf… I think I get why."

"Yeah…" Toola nodded, excited and a little breathless. Already pent up, she squirmed in delight, Amethyst gyrating her hips and grinding their sexes together. The mare savored the sweet contact of a soft filly pussy on her vulva. Toola Roola was visibly in bliss, and Amethyst realized she was giving this cute foal her very first time. She was taking her virginity, and she gave her her best.

*Shlick-shlick-shlick!*

The wet sound of their mating filled the room, along with the scent of excited mares. Amethyst let herself go, having sex with this young filly, and fully enjoying it. Her chest heaved from the exertion, her heart thundering as if she was galloping a mare-a-thon.

Suddenly, Toola cried out, and she came. Fillycum gushed from her little pussy, coating Amethyst's marehood in gooey secretions. The unicorn didn't stop, instead feverishly rubbing herself on the climaxing filly, taking her pleasure from the foal. Toola wasn't minding it, of course, the nonstop stimulation giving her orgasm after orgasm.

With a loud gasp, Amethyst Star mashed her pussy on Toola Roola's throbbing mound, and came as well. “Unf! Aaah!” Tremors rocked her entire body, her vagina and womb shuddering from her orgasm. Their clits pulsed against each other, sending tingly shocks of intense pleasure through their spines. Finally too sensitive to continue, Amethyst backed away, filaments of marecum and fillycum linking their vulvas before snapping.

The unicorn fell on her back, gasping, butt-to-butt with her young partner. She relaxed, her tail intertwining with Toola Roola’s own short blue one as they both came down from their peaks.

The filly shifted around to face Amethyst. The mare embraced her, wrapping her forelegs around Toola Roola’s neck. She nuzzled the foal’s sweaty, disheveled mane, planting a flurry of little kisses on her forehead and making her giggle.

“Mmmh… That felt sooo good,” Amethyst whispered, her mind clouded in post-orgasmic bliss.

“Uh-uh…” the filly half-responded, the sound of her voice barely audible in her afterglow.

Amethyst caressed her colorful mane. “Was having sex with another girl as good as you imagined?”

Slowly, a grin of deep satisfaction formed on Toola’s lips. “Yeah, better…”

“Wanna do it again?”

Toola Roola canted her head, staring wide eyed at the unicorn. “Can we?”

“Heheh, sure! As many times as you can handle. We have all night…” Seeing the filly’s eyes sparkle in excitement, Amethyst kissed her on the lips, making out sloppily with her. Moving lower down her little body, Amethyst gazed upon her puffy fillyhood, licking her lips in anticipation.

“Your turn now,” the mare said, before plunging tongue first in her little pussy.

~ ✭ ~

The next morning, Toola Roola woke up in Amethyst Star’s bed, snuggled close to the unicorn, her face caressed by the sleeping mare’s silky mane. With a happy sigh, the filly gently stroked Amethyst’s magenta fur, taking comfort in the regular heartbeat she felt under it. Her fluffy coat smelled of sweat and sex, reminding her of all the amazing things they’d done together.

Staying still, waiting for Amethyst to wake up, Toola Roola felt like a brand new filly. Her sexual orientation had made her uncomfortable for years, but all that paled under the delightful wonders she’d shared with the mare. For the first time ever, she realized she actually wanted her friends to know about it, to know she loved other fillies, and that it was great.

Toola Roola thought about her best friend, Coconut Cream. She wanted to tell her how she really felt… and maybe even give her a hooves-on introduction. She smiled at the naughty thought.